The Esquire Guy’s Guide to Asking for Advice

First of all, we have to come up with a better word for whatever this is. Brain-picking sounds like a medieval surgeon’s treatment for foot cramps. It sounds misguided and painful. Probably lethal. And it’s a strangely off-putting term for what is almost always a delightful experience, both for the picker and the pickee. (Which are also off-putting terms, and which I won’t be using again.)

How to Pick a Brain

Key Technical Matters

Never ask for more than 15 minutes of a person’s time. You’ll probably end up with 30, but never ask for more than 15.

When making a brain-picking request, frame it in terms of your subject: “I’d like to ask you about your career.” Not “I’d like to ask you about my career.”

Be as accommodating as possible: “I’m available next week.” Not “I’m available Thursday.” And definitely not “I can squeeze you in from 8 to 8:15.”

Be courteous: “I would be grateful for your time.” Not “You gotta help me out here.”

And certainly not: “YOU GOTTA HELP ME OUT HERE!”

There’s no need to praise the person. Your request to pick their brain is praise enough.

Never ask a mentor to help you make a decision. Consultants make decisions. Which is why consultants get paid. Mentors give feedback.

Be grateful but not obsequious. You’re not beneath the other person. You’re just a little less experienced in a certain category of business.

Remember that they’re getting something out of it, too: flattery. And possibly a free coffee or something. But mainly flattery.

Remember to listen more than you talk.

And never interrupt.

But don’t just sit there.

Really. Don’t just sit there.

… [PAUSE]

For the love of god, ask a question!

The first rule of brain-picking: It shouldn’t require your mentor to actually think. You should ask only for something that is pre-made and ready to be handed over: basic knowledge. What the service does not include is recommendations. Brain-picking is meant to be a passive exercise on the expert’s part. If you’re asking for recommendations, then you are forcing your subject to work. Offering a recommendation involves analysis and decision-making. Decisions are hard. Decisions are work.

Don’t ask your subject if you should switch careers. Ask about the career you’re considering switching to. Don’t ask your subject if you should go work for so-and-so. Ask your subject what kind of person so-and-so is to work for. Don’t ask your subject if you may go to the restroom. Ask your subject if he or she knows where the restrooms are. (You really should’ve taken care of this before the meeting.) Ask questions that are easy to answer but that you just don’t know the answer to.

Keep it short. Request about 15 minutes of their time. You’ll probably get 30, but ask for 15. Says Alex Iskold, founder and CEO of GetGlue, a social network for TV, movie and sports fans: “If someone asks me for something that’s in my area of expertise, and if it’s someone I know or someone referred to me by someone I know, and it’s 10, 15 minutes, half an hour, I think that’s reasonable and totally fine, and if I have the time, I’m happy to be helpful. It’s all about time.”

Before making the request, ask yourself why this person would want to help you. The answers should be: because it will be easy, because you want to do what they do at some point in your career, because it allows them to do a generous thing and because whatever mutual connection you share is an important one (you went to the same school, you work in the same building, you were at the same conference, you both seem to enjoy doing inventory). The point is to give them a reason to help you.

“I tend to prioritize people in college who are trying to become their own entrepreneurs. It’s a personal preference; these are people that inspire me,” says Chantel Waterbury, founder and CEO of Chloe + Isabel, a New York-based jewelry company. “And if someone needs branding advice or design or product-development advice, I always take those calls, because I know it’s an area in which I can add a lot of value.”

What Brain-picking Means to the Mentor

The main force at work with brain-picking could be described as the ecstasy of consultancy–an unacknowledged but crucial factor in business. The one being consulted gets to yammer on in relatively simple terms about something involving their area of expertise. Which is easy and fun. (There is nothing more satisfying than being the smartest person in the room, especially if the room has only two people.) Says Waterbury: “There are people I reach out to who are extremely seasoned and working in their industry for 40, 50 years, and I feel sometimes like it’s a one-way street, and I apologize, and they’ve said to me, ‘I do this because it invigorates me.’ I have to remind myself that they are in fact getting something from it, and I’m not just taking.”

How to Ask Questions

Questions should begin with phrases like:
Could you tell me about …
How did you …
When you were in my position …

Questions should not begin with phrases like:
Can I have …
Can you help me…
Will you excuse me while I tweet that I’m hanging out with you …

Questions should never, under any circumstances, contain the following:
If you’ll allow me to tell you the story of my career. It all started …
What, you think you’re better than me or something?
Now for the lightning round …
Can I just have a damn job, dude?

The ecstasy of consultancy is really just a “social reward,” as the psychologists put it. Social rewards are powerful things.

“We know that when you share your experience with someone else, then you activate the default network in the brain, which is associated with a sense of social connection, empathy and positive reward,” says Anthony I. Jack, assistant professor of cognitive science, philosophy and psychology at Case Western Reserve University. When your brain is being picked, he adds, “this network comes up, and the analytic/critical thinking network gets suppressed, and you’re engaged.”

Brain-picking is a form of “inter-subjectivity,” the shared exploration by two people of each other’s experiential world. You’re getting social capital, but you’re sharing social capital, too.

The reason this kind of reward is so powerful–and the reason why brain-picking has become an important part of business–is that you’re allowing another person to personally invest in your success, if only temporarily. This is an honor. And it’s uniquely flattering. Requests for consultancy could be considered the most important measure of success. That’s a powerful gift you’re giving someone. Brain-picking is an even trade.